2047-91-8

Basic information

• Product Name: 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE
• Synonyms: TETRAHYDROCYCLOPENT(B)INDOLE;2,3-Trimethyleneindole;NSC 112674;1,2,3,4-Tetrahydrocyclopent[b] indole 96%
• CAS NO: 2047-91-8
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.21
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 2047-91-8.mol

Chemical Properties

• Melting Point: 100.5-105.5 °C(lit.)
• Boiling Point: 300.9 °C at 760 mmHg
• Flash Point: 130.4 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: 1.701
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 17.83±0.20(Predicted)
• CAS DataBase Reference: 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE(2047-91-8)
• EPA Substance Registry System: 1 2 3 4-TETRAHYDROCYCLOPENT(B) INDOLE(2047-91-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2047-91-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1,2,3,4-Tetrahydrocyclopent[b]indole is used as a reactant for the synthesis of BACE inhibitors, which are potential treatments for Alzheimer's disease. It is also used to synthesize benzazocinecarboxylic acids, which have potential anti-inflammatory properties.
2. Used in Organic Chemistry:
1,2,3,4-Tetrahydrocyclopent[b]indole serves as a reactant for thionium species-mediated functionalization at the 2α-position of indoles, allowing for the creation of new compounds with specific functional groups.
3. Used in Oxidation Reactions:
In the field of organic chemistry, 1,2,3,4-Tetrahydrocyclopent[b]indole is used as a reactant for the preparation of tetramethylpiperidine-1-oxoammonium salts, which act as oxidants in various chemical reactions. These oxidants can be employed in the synthesis of different organic compounds and materials.

InChI:InChI=1/C11H11N/c1-2-6-10-8(4-1)9-5-3-7-11(9)12-10/h1-2,4,6,12H,3,5,7H2

Upstream product

• 60-29-7 diethyl ether 
• 1132-58-7 cyclopentanone phenylhydrazone 
• 53512-39-3 8b-methylsulfanyl-1,2,3,8b-tetrahydro-cyclopenta[b]indole 
• 78839-81-3 (3aS,8bR)-2,3,3a,4-Tetrahydro-1H-cyclopenta[b]indol-8b-ol 
• 107097-16-5 1-(1-benzotriazolyl)cyclopentene 
• 120-92-3 cyclopentanone 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 443303-78-4 2-(2-nitrophenyl)-2-cyclopenten-1-one 
• 2727-71-1 N-(2-bromophenyl)-2,2,2-trifluoroacetamide 
• 694-28-0 2-chlorocyclopentanone 
• 609-73-4 o-nitroiodobenzene 
• 6293-63-6 (o-nitrophenyl)phenyliodonium iodide 
• 244785-24-8 C₁₁H₁₁NO₃ 

Downstream Products

• 919119-69-0 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole 
• 96463-98-8 2-cyclopent-1-enyl-N,N-dimethyl-aniline 
• 100617-05-8 2-cyclopentyl-N,N-dimethyl-aniline 
• 1070731-40-6 1,2,3,4-tetrahydro-4-(3,5-dimethylphenyl)cyclopenta[b]indole 
• 1180557-84-9 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydrocyclopenta[b]indole 
• 1313809-57-2 3-methoxy-4-(4-methoxybenzyl)-1,2,3,4-tetrahydrocyclopenta[b]indole 
• 1313809-71-0 4-(4-methoxybenzyl)-1,2,3,4-tetrahydrocyclopenta[b]indole 
• 652145-29-4 3-{1,2,3,3a,4,8b-hexahydro-4-[4-(2,2-diphenylvinyl)phenyl]cyclopenta[b]indole-7-yl}-2-cyanoacrylic acid 
• 652145-28-3 D₁₀₂ 
• 786643-20-7 D₁₄₉ 
• 652145-27-2 1,2,3,3a,4,8b-hexahydro-4-[4-(2,2-diphenylethenyl)phenyl]cyclopenta[b]indole-7-carboxaldehyde 
• 1448447-01-5 N-benzyloxycarbonyl-1,2,3,4-tetrahydrocyclopenta[b]indole 

Relevant articles and documents

Marked effects of indolyl vs. indolinyl substituent on solid-state structure, carrier mobility and photovoltaic efficiency of asymmetrical squaraine dyes

Two solution-processed asymmetrical squaraines (ASQs) with cyclopenta[b]indolinyl (1a) and cyclopenta[b]indolyl (1b) as end cappers have been designed and synthesized. Although the internal molecular structure variations are minimal, the presence of the cyclopenta[b]indolinyl group endows 1a more planar molecular structure, which results in a much more compact solid-state structure (density is 1.317 g cm-3 for 1a but is 1.187 g cm-3 for 1b), dramatically affecting charge transport in the thin films. The hole mobility of 1a:PC71BM blended film is about 7 times higher than that of 1b:PC71BM. Consequently, the maximum power conversion efficiency (PCE) value of the organic photovoltaic cells (OPVs) based on 1a of up to 4.1%, approximately 80% higher than that of 1b, is one of the highest PCEs achieved for ASQ-based bulk-heterojunction (BHJ) OPVs. This journal is

A process for the preparation of 1,2,3,4,8,9,10,10a-octahydro-7bH- cyclopenta[b][1,4]diazepino[6,7,1-hi]indole

A synthesis of 1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta[b][1,4] diazepino[6,7,1-hi]indole is described exemplifying a new synthetic route to medicinally interesting compounds. The key step involves a cyclization of 2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)-ethanamine with aqueous formaldehyde in the presence of trifluoroacetic acid.

One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles

A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Soluble asphaltene oxide: A homogeneous carbocatalyst that promotes synthetic transformations

Carbocatalysts, materials which are predominantly composed of carbon and catalyze the synthesis of organic or inorganic compounds, are promising alternatives to metal-based analogues. Even though current carbocatalysts have been successfully employed in a broad range of synthetic transformations, they suffer from a number of drawbacks in part due to their heterogeneous nature. For example, the insolubility of prototypical carbocatalysts, such as graphene oxide (GO), may restrict access to catalytically-active sites in a manner that limits performance and/or challenges optimization. Herein we describe the preparation and utilization of soluble asphaltene oxide (sAO), which is a novel material that is composed of oxidized polycyclic aromatic hydrocarbons and is soluble in a wide range of organic solvents as well as in aqueous media. sAO promotes an array of synthetically useful transformations, including esterifications, cyclizations, multicomponent reactions, and cationic polymerizations. In many cases, sAO was found to exhibit higher catalytic activities than its heterogeneous analogues and was repeatedly and conveniently recycled, features that were attributed to its ability to form homogeneous phases.

Pd-Catalyzed Dearomatization of Indole Derivatives via Intermolecular Heck Reactions?

Pd-catalyzed intermolecular dearomative Heck reaction of indoles with aryl iodides is described. The challenges on both reactivity and regioselectivity are addressed by the judicious regulation of the geometric and electronic properties of the substrates. An array of indoline derivatives bearing C2-quaternary center is obtained in good to excellent yields (up to 93%) with exclusive regioselectivity under operationally simple conditions. The mechanistic proposal is supported by detailed DFT calculations.

Supported dual-acidic 1,3-disulfoimidazolium chlorozincate@HZSM-5 as a promising heterogeneous catalyst for synthesis of indole derivatives

HZSM-5-supported Br?nsted and Lewis acidic ionic solid 1,3-disulfoimidazolium chlorozincate materials ([dsim]2[ZnCl4]@HZSM-5) were synthesized with various ratios (3, 6, 9, 17 and 50% w/w). The heterogeneous materials were characterized via a variety of spectroscopic techniques. Dual acidity of these materials was determined using specified techniques. These acidic solids were examined as stable heterogeneous catalysts for the Fischer indole reaction of equimolar amounts of phenylhydrazine hydrochloride and various aliphatic or aromatic ketones at 80–90°C in neat condition to produce substituted indole derivatives. The efficient 17% ionic salt-loaded HZSM-5 composite was easily reused for ten consecutive cycles with a slight loss of its activity. The recycled catalyst was further analysed using powder X-ray diffraction and inductively coupled plasma optical emission spectrometric techniques.

INDOLINE DERIVATIVE AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

The present invention relates to an indoline derivative, capable of reducing dark current in a device, and to an organic electronic device including the same. The indoline derivative is represented by chemical formula 1. In the chemical formula 1, L1 is a

An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C?H Amination

A new homogeneous bromine(?I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C?H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C?N bond formation, including its application in the synthesis of alkaloid building blocks. This aspect is demonstrated by a new synthetic approach to aspidospermidine. In addition to the development of the catalyst system, the structures of the involved bromine(I) key catalysts were fully elucidated, including by X-ray analyses.

Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides

Catalytic asymmetric N-alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza-para-quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N-protective group, the intermolecular C?N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.